Founding Operations Associate

About Terminal Terminal builds telematics data infrastructure for the commercial fleet industry. Commercial auto insurers and fleet software companies, including industry leaders like Intact Insurance, Penske, and Progressive, depend on our platform to access GPS, speeding, and vehicle data from 330+ telematics providers. We recently raised our Series A led by Battery Ventures and are backed by Y Combinator, Golden Ventures, Penske Transportation Solutions, and Intact Private Capital. Our team works together in person in Toronto, combining early-stage speed with late-stage maturity while processing many terabytes of vehicle data every day. For more on working at Terminal, see our careers page at withterminal.com/careers . This role is only open to Toronto/GTA-based candidates. About the role Help build how Terminal runs. You'll work directly with our Chief of Staff to solve operational problems, drive cross-functional projects, and build reliable systems across workplace, people, events, and finance. This role combines analytical judgment with hands-on ownership, from identifying a problem to making the solution work. What you’ll do 1. Run workplace operations Make our HQ somewhere people love to show up to every day. You’ll be the go-to for all things related to our office in King West. You’ll maintain established vendor relationships, coordinate with building management, and ensure our office is stocked across IT, supplies and snacks. 2. Deliver awesome events We have two offsites a year for our team, and you’ll work with our team leads and travel vendors to plan and execute each one. To support our recruiting efforts, you’ll be hosting events to attract the best talent in the city. You’ll also own hosting customer-centric events, such as dinners, roundtables, and visits. You’ll build repeatable plans so we can scale our internal and external events. 3. Drive People and hiring processes We’re growing fast, and you’ll support onboarding our newest team members, making sure every step of their journey is smooth, from systems access to the onboarding plan. You’ll also support recruiting workflows, interview scheduling, and offer preparation, partnering with talent leads. 4. Support finance operations You’ll help make sure our customers are billed correctly and pay on time, while also making sure we pay our bills on time. That means executing accounts payable, vendor onboarding, expense tracking, billing reviews, and collections outreach. 5. Drive system and process documentation As the team and company scale, you’ll establish standard operating procedures, maintain our Terminal handbook, and use AI and automation to increase efficiency across the business and your focus areas. What we’re looking for A strong operational background: 2–5 years across business operations, People ops, events management, or a startup generalist role, with clear examples of workflows you executed through end-to-end implementation rather than pure coordination. Ownership without a playbook: You diagnose messy operational challenges, build structured systems, and keep them running dependably. Detail and follow-through: You maintain a high bar for accuracy across task lists, vendor management, calendar logistics, and confidential HR records. Influence and judgment: You align people smoothly across talent, engineering, and leadership teams to drive outcomes without requiring formal authority. Systems and data fluency: You are skilled in spreadsheets, HR platforms like Rippling, Slack, and document hubs (Notion/Drive), leveraging AI tools thoughtfully to multiply productivity. Tools you’ll be using: Claude, Rippling, Ashby, Notion, Venn, Measure and Slack. Bonus points You've helped build a function or company from scratch, supported People, hiring, finance, or events systems at an early-stage startup, and regularly used AI to automate work your team was doing by hand. What success looks like In the first 90 d